Acetic Acid → 1-Benzyl-8-cyano-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid (pyridin-4-ylmethyl)-amide

HRID 919732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 919732
C[O:2][C:3]([C:5]1[C:6]([OH:31])=[C:7]2[C:12](=[C:13]([C:15]#[N:16])[N:14]=1)[N:11]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:10](=[O:24])[C:9]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[CH:8]2)=O.[NH2:32][CH2:33][C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1.CC(O)=O.O>CCO>[N:37]1[CH:38]=[CH:39][C:34]([CH2:33][NH:32][C:3]([C:5]2[C:6]([OH:31])=[C:7]3[C:12](=[C:13]([C:15]#[N:16])[N:14]=2)[N:11]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:10](=[O:24])[C:9]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:8]3)=[O:2])=[CH:35][CH:36]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 962WaterHCID 773174-PyridinemethanamineHCID 682976531-Benzyl-8-cyano-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

Produkt 1

HCID 867141111-Benzyl-8-cyano-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid (pyridin-4-ylmethyl)-amideAusbeute 43,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1-benzyl-8-cyano-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (35 mg, 0.085 mmol) and 4-(aminomethyl)-pyridine (0.030 mL, 0.30 mmol) in 2 mL of EtOH was refluxed for 16 h. AcOH (0.1 mL) and water (4 mL) were added, and the resulting precipitate was isolated by filtration. The crude solid was purified by silica gel chromatography (0-45% EtOAc/CH2Cl2+1% AcOH) to give 18 mg of the title compound as an off-white solid. MS: (+) m/z 488.13 (M+1).

Aufarbeitung

  1. temperaturewas refluxed for 16 h
  2. customthe resulting precipitate was isolated by filtration
  3. customThe crude solid was purified by silica gel chromatography (0-45% EtOAc/CH2Cl2+1% AcOH)

Quellen und Nachweise

ORD-Eintrag
ord-aee9d31f1e5a48a9989b3f97952c2a18
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09271970B2

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